1-methyl-1H-indole-2,3-dione 3-hydrazone | 3265-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-methyl-1H-indole-2,3-dione 3-hydrazone
• 英文别名: 3-hydrazinylidene-1-methylindol-2-one
• CAS: 3265-23-4
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: WEJSLWMWNXETNI-UHFFFAOYSA-N

物化性质

• 熔点：
  104-106 °C
• 沸点：
  342.9±25.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-methyl-1H-indole-2,3-dione 3-hydrazone 在 (2-hydroxyphenyl)oxoacetic acid 作用下， 以 甲苯 为溶剂， 生成 bis-(1-methyl-2-oxo-indolin-3-ylidene)-hydrazine
  参考文献：
  名称：

  Synthesis of 3-(2-Oxo-2,3-dihydrobenzo[b]furan-3-ylidenehydrazono)-2,3-dihydrobenzo[b]furan-2-one

  摘要：

  Reactions of benzophenone and fluoren-9-one hydrazones with (2-hydroxyphenyl)oxoacetic acid gave [carboxy(2-hydroxyphenyl)methylidenehydrazono](2-hydroxyphenyl)acetic acid which underwent intramolecular cyclization with formation of 3-(2-oxo-2,3-dihydrobenzo[b]furan-3-ylidenehydrazono)-2,3-dihydrobenzo[b]furan-2-one. The symmetric azine was also obtained by reactions of (2-hydroxyphenyl)oxoacetic acid with triphenylphosphoranylidenehydrazones derived from benzophenones, fluoren-9-one, and 1-methyl-2,3-dihydro-1H-indole-2,3-dione.

  DOI：

  10.1134/s1070428007060103
• 作为产物：
  描述：

  靛红 在 hydrazine hydrate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.51h， 生成 1-methyl-1H-indole-2,3-dione 3-hydrazone
  参考文献：
  名称：

  Microwave Synthesis, Characterization, and Antimicrobial Activity of Some Novel Isatin Derivatives

  摘要：

  三系列吲哚啉衍生物[3-肼基，3-硫脲基和3-亚胺羧酸衍生物]利用微波辐射合成。制备的化合物通过FT-IR、NMR、元素分析和X射线晶体学对衍生物5b进行表征。合成的化合物对选定的细菌和真菌进行抗菌活性筛选。结果显示，N-烷基吲哚啉衍生物具有不同谱活性。大多数3-肼基和3-硫脲基吲哚啉衍生物在生物学上无活性，通常活性衍生物对革兰氏阳性细菌表现出弱到中等的活性。亚胺吲哚羧酸衍生物（2-[4-(1-苄基-5-溴-2-氧吲哚-3-基亚胺基)苯基]乙酸，5d）对所有经测试的革兰氏阳性细菌和真菌病原体表现出有希望的活性。

  DOI：

  10.1155/2015/716987

文献信息

• Iodine mediated propargylic substitution/aza-Meyer–Schuster rearrangement: stereoselective synthesis of conjugated unsymmetrical azines
  作者：Sengodagounder Muthusamy、Karuppu Selvaraj、Eringathodi Suresh

  DOI：10.1016/j.tetlet.2016.09.055

  日期：2016.10

  A facile synthesis of highly substituted as well as conjugated unsymmetrical azines via the reaction of propargyl alcohols and isatin hydrazones in the presence of iodine is demonstrated under open to air. A series of unsymmetrical azines have been synthesized with excellent yields from simple and readily available starting materials in a complete stereoselective manner.

  在空气存在下，通过炔丙醇与靛红在碘存在下的反应，可以轻松合成高度取代的共轭不对称杂志。从简单易用的起始原料以完全的立体选择性方式合成了一系列不对称的嗪，收率很高。
• Transformation of Isatin 3-Acylhydrazones under Acetylating Conditions: Synthesis and Structure Elucidation of 1,5′-Disubstituted 3′-Acetylspiro[oxindole-3,2′-[1,3,4]oxadiazolines]
  作者：László Somogyi

  DOI：10.1246/bcsj.74.873

  日期：2001.5

  Several substituted isatin 3-acylhydrazones (e.g. 1a–k, n, p, t) have been synthesized. Under acetylating conditions they were transformed into selectively acetylated derivatives (e.g., 1l, n, o, q–s) and into the novel, title spiroheterocycles (2a–i). Some side reactions occurring under various acetylating conditions are also discussed.

  合成了几种取代的异香豆酸3-酰基肼（例如1a–k、n、p、t）。在乙酰化条件下，它们转化为选择性乙酰化的衍生物（例如1l、n、o、q–s）以及新型的标题螺旋杂环（2a–i）。还讨论了在不同乙酰化条件下发生的一些副反应。
• Synthesis, Characterization and Anticancer Activity of (5,1-Substituted)-3-(indoline-4-(thiophene-2-yl-methylene)-2-(p-tolyl)-2-methylene)-4,3-dihydro-1H-imidazole-5-one Derivatives
  作者：Chandraprakash Bayya、Sarangapani Manda

  DOI：10.14233/ajchem.2021.23271

  日期：——

  The synthesis of novel imidazole-5-one derivatives (5a-j) was allowed in a conventional method by way of Erlenmeyer and Schiff base mechanism. Compound 2a was synthesized by Erlenmeyer reaction of N-(4-methoxy benzoyl)glycine with 2-thiophene-carboxaldehyde in the presence of acetic anhydride and anhydrous sodium acetate. Finally, it undergoes dehydration reaction with Schiff bases of isatin derivatives

  新型咪唑-5-酮衍生物(5a-j)的合成可以通过常规方法通过Erlenmeyer和Schiff碱机理进行。化合物2a是通过N-(4-甲氧基苯甲酰基)甘氨酸与2-噻吩甲醛在乙酐和无水乙酸钠存在下进行Erlenmeyer反应合成的。最后与靛红衍生物(4a-j)的席夫碱进行脱水反应，得到最终化合物5a-j。通过MTT测定方法评价了新合成的5-咪唑酮衍生物的有机潜力其体外抗癌活性。它针对 MCF-7 细胞，与阿霉素流行药物进行比较。合成的化合物5e、5f和5j对MCF-7细胞系表现出优异的抗癌活性。
• New method for the preparation of 3-diazo-1,3-dihydroindol-2-ones
  作者：V. M. Muzalevskiy、E. S. Balenkova、A. V. Shastin、A. M. Magerramov、N. G. Shikhaliev、V. G. Nenajdenko

  DOI：10.1007/s11172-011-0359-5

  日期：2011.11

  A new method for the preparation of diazo compounds of 2-indolinone series by oxidation of isatin hydrazones with polyhaloalkanes in the presence of copper salts in catalytic amounts was developed.

  开发了一种新方法，通过在催化量的铜盐存在下，用多卤烷氧化异吲哚酮肼，制备2-吲哚酮系列的偶氮化合物。
• Squaramide-catalyzed asymmetric Mannich reactions between 3-fluorooxindoles and pyrazolinone ketimines
  作者：Qing-Da Zhang、Bo-Liang Zhao、Bing-Yu Li、Da-Ming Du

  DOI：10.1039/c9ob01350d

  日期：——

  An enantioselective Mannich reaction between 3-fluorooxindoles and pyrazolinone ketimines has been developed for the construction of amino-pyrazolone-oxindoles containing stereogenic C-F units. Based on this new protocol that allows for the generation of two adjacent tetrasubstituted stereocenters, a variety of structurally diverse fluorinated amino-pyrazolone-oxindoles were obtained in good to excellent

  已经开发了3-氟代羟吲哚与吡唑啉酮酮亚胺之间的对映选择性曼尼希反应，用于构建含有立体异构CF单元的氨基-吡唑啉酮-羟吲哚。基于允许产生两个相邻的四取代的立体中心的新方案，获得了各种结构多样的氟化氨基吡唑啉酮-羟吲哚，收率高至优异，具有出色的非对映选择性和对映选择性（高达98％的收率，> 20：1博士和> 99％ee）。此外，在克级反应中获得了良好的产率和高的立体选择性。